Cyanogen Bromide → 1'-Cyano-1-(2-fluorophenyl)spiro[indoline-3,4'-piperidine]

HRID 1702018Notes

Reaction equation

HRID 1702018 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH2:9]1.[N:23]#CBr.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:16]([N:13]1[CH2:14][CH2:15][C:10]2([C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[CH2:9]2)[CH2:11][CH2:12]1)#[N:23]

Participants

5

Reactant 3

HCID 10476Cyanogen Bromide2×HCID 11430Potassium CarbonateHCID 128015941-(2-Fluorophenyl)-1'-methylspiro-[indoline-3,4'-piperidine]

Product 1

HCID 128016141'-Cyano-1-(2-fluorophenyl)spiro[indoline-3,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.82 g of 1-(2-fluorophenyl)-1'-methylspiro[indoline-3,4'-piperidine], free base of Example 10, 0.92 g of cyanogen bromide and 1.0 of potassium carbonate in 24 ml of methylene dichloride is stirred at ambient temperature for 5 hours and then an additional 0.20 g of cyanogen bromide is added. Stirring is continued for 16 hours before filtering the mixture. The filtrate is boiled with methyl alcohol and the hot solution is evaporated to dryness leaving a brown foam. This product is purified by passing through a silica gel column, ether methylene chloride (1:1) mixture eluant, to provide a tan solid. The solid is recrystallized from an acetone-hexane mixture to provide white needles (slight tan tint), mp 131°-132° C. of 1'-cyano-1-(2-fluorophenyl)spiro[indoline-3,4'-piperidine].

Workup

  1. stirringStirring
  2. waitis continued for 16 hours
  3. filtrationbefore filtering the mixture
  4. customthe hot solution is evaporated to dryness
  5. customleaving a brown foam
  6. customThis product is purified
  7. customto provide a tan solid
  8. customThe solid is recrystallized from an acetone-hexane mixture

Sources & evidence

ORD record
ord-c86aaede1ea04923b984ab916d428fd0
Source dataset
uspto-grants-1983_04
Patent number
US04379932

Reaction notes

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